Milwaukee Bucks: Revisiting the Damian Lillard Trade As Star PG’s Time in Milwaukee Unceremoniously Ends After Just 2 Seasons

Damian Lillard’s Forgettable Milwaukee Bucks Career

Damian Lillard was shockingly released by the Milwaukee Bucks as the 2025 free agency cycle began, as the team essentially swapped the injured point guard for free agent center Myles Turner. With Lillard’s salary spread over the next five seasons, the team opened up cap room to add Turner. The move has puzzled fans and former players alike.

In July 2023, the Bucks traded Jrue Holiday, Grayson Allen, and three unprotected first round picks, including the 2029 first round pick and pick swaps in 2028 and 2030. Many experts graded the move very favorably for Milwaukee, and U.S. sportsbooks were updated to have the Bucks as the odds-on favorites to win the 2024 NBA Championship. The two-man game between Lillard and Giannis Antetokounmpo was set to dominate the league.

Two years later, Lillard is gone after having played just three total playoff games with Antetokounmpo, all of which Lillard was far from himself due to coming back from a serious shoulder issues, and the last of which saw him play just six minutes before tearing his ACL.

Revisiting the Value Milwaukee Gave Up for Damian Lillard

In 2023, Milwaukee gave up Holiday, the third and  most underrated part of the big three that won them the 2021 NBA Championship, Allen, a strong role player, and three significant picks. Given that Lillard has now been released to make way for Turner, the Bucks have now essentially traded Holiday, Allen, and three firsts for Turner. This is not a deal that has aged well.

Portland would soon move Holiday to Boston, where he would win another NBA Championship in 2024, and, just days before Lillard’s release from Milwaukee, Portland would reacquire Holiday in a trade with the Celtics. The Blazers now have Holiday joining a strong defensive team that includes Toumani Camara, a player they added from the Phoenix Suns in part of the Lillard deal.

In 2023, CBS Sports had this to say about Antetokounmpo and Lillard:

“Ideally, this trade will ensure Antetokounmpo signs another contract with the team that drafted him 10 years ago and give the entire franchise a sense that it is cooking up something special rather than trying to reheat something stale.”

In 2025, the Bucks have failed to achieve this ideal. The franchise is now in their “reheat mode” and desperately trying to ensure Antetokounmpo believes in the group surrounding him.

With hindsight, the Lillard move has proved to be disastrous. Of course, the true value of the deal won’t be known until the 2028, 2029, and 2030 picks are used. Regardless, it already is clear that Milwaukee is a big loser in the trade.